This book explores the masculinity and sexuality of migration, analyzing the complex processes of becoming a man and the strategies used by men to reconcile paradoxes and contradictions that co-exist between multiple masculinities and contradictory models of being a man. Vasquez del Aguila offers a number of conceptual contributions, including the notion of “masculine capital” that provides men with the necessary “masculine” skills and cultural competence to achieve legitimacy and social recognition as men; an analysis of male friendship where notions of solidarity and intimacy co-exist with those of distrust, competition, and power relations; and three social representations of being a man: the winner, the failed, and the good enough man. By analyzing heterosexual as well as gay masculinities, and incorporating race and class relations, this study shows the multiplicity and hierarchies of masculinities presented within a particular cultural context. Through ethnographic research undertaken over more than four years in New York and Lima, Peru, this book also examines the role of the Internet and transnational romances and the ways in which migration can create new opportunities for male sexual intimacy, while for others, it creates loneliness and isolation.